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Compounds Containing Nitrogen question

2007 · Shift 0 · Q17
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Compounds Containing Nitrogen question

2007 · Shift 0 · Q17

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Which one of the following is the strongest base in aqueous solution?
  1. A
    Trimethylamine
  2. B
    Aniline
  3. C
    Dimethylamine
  4. D
    Methylamine
View written solutionFree

Correct answer: C

  1. Concept used: In aqueous solution, the basic strength of amines depends on:

    • the +I+I+I effect of alkyl groups, which increases electron density on nitrogen and makes it more basic,
    • solvation of the protonated amine in water, which stabilizes the conjugate acid.
  2. Compare the given amines:

    • Aniline (C6H5NH2\mathrm{C_6H_5NH_2}C6​H5​NH2​): The lone pair on nitrogen is delocalized into the benzene ring by resonance, so it is much less available for protonation. Hence, aniline is the weakest base here.
    • Methylamine (CH3NH2\mathrm{CH_3NH_2}CH3​NH2​): A primary aliphatic amine. The methyl group gives a +I+I+I effect, increasing basicity compared to ammonia.
    • Dimethylamine ((CH3)2NH\mathrm{(CH_3)_2NH}(CH3​)2​NH): A secondary amine. Two methyl groups increase electron density on nitrogen, and in aqueous solution its conjugate acid is still reasonably well solvated. This makes it very basic.
    • Trimethylamine ((CH3)3N\mathrm{(CH_3)_3N}(CH3​)3​N): Though it has three methyl groups giving strong +I+I+I effect, in aqueous solution the protonated form (CH3)3NH+\mathrm{(CH_3)_3NH^+}(CH3​)3​NH+ is less effectively solvated due to steric hindrance. So it is less basic than dimethylamine in water.
  3. Order of basic strength in aqueous solution: (CH3)2NH>CH3NH2>(CH3)3N>C6H5NH2\mathrm{(CH_3)_2NH > CH_3NH_2 > (CH_3)_3N > C_6H_5NH_2}(CH3​)2​NH>CH3​NH2​>(CH3​)3​N>C6​H5​NH2​

  4. Therefore, the strongest base in aqueous solution is: Dimethylamine\boxed{\mathrm{Dimethylamine}}Dimethylamine​

  5. Option check:

    • A: Trimethylamine — Incorrect
    • B: Aniline — Incorrect
    • C: Dimethylamine — Correct
    • D: Methylamine — Incorrect
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